When I went to investigate this, I tested how a lot of user agents currently handle their numbering rules, and none of them match the current spec. (and very few come close to the spec. or each other, and no major ones match each other exactly).

Results

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Sample Ordered List Value Attributes
MarkupHTML5IEGeckoWebkitPrestoLynxw3mDillo
<li ></li> 1 1 1 1 1 1 1 1
<li value="0" ></li> 0 2 0 2 0 0 0 0
<li value="1" ></li> 1 1 1 1 1 1 1 1
<li value="3a" ></li> 3 1 3 3 3 3 3 3
<li value="3b" ></li> 3 1 4 3 3 3 3 3
<li value="2 " ></li> 2 2 2 2 2 2 2 2
<li value="2 1"></li> 2 2 2 2 2 2 2 2
<li value="2.1"></li> 2 2 2 2 2 2 2 2
<li value=".2" ></li> 3 3 2 3 0 3 0 0
<li value="-3" ></li>−3 3 0 4−3−3 0 0
<li value="+3" ></li> 3 3 3 3 3−2 3 3
<li value="-3" ></li>−3 4 0 4−3−3 0 0
<li value="" ></li>−2 1 1 5 0−2 0 0
<li ></li>−1 2 2 6 1−1 1 1
<li value="" ></li> 0 1 3 7 0 0 0 0
<li value="4" ></li> 4 4 4 4 4 4 4 4
<li value="5" ></li> 5 5 5 5 5 5 5 5
<li ></li> 6 6 6 6 6 6 6 6
<li value="c" ></li> 7 1 7 7 0 7 0 0

Details

IE

Gecko

Webkit

Presto

Lynx

w3m

Dillo

Notes

Personally, I don't have a solution to propose; this is purely informative.